CA2320354A1 - Novel compounds and their use as positive ampa receptor modulators - Google Patents
Novel compounds and their use as positive ampa receptor modulators Download PDFInfo
- Publication number
- CA2320354A1 CA2320354A1 CA002320354A CA2320354A CA2320354A1 CA 2320354 A1 CA2320354 A1 CA 2320354A1 CA 002320354 A CA002320354 A CA 002320354A CA 2320354 A CA2320354 A CA 2320354A CA 2320354 A1 CA2320354 A1 CA 2320354A1
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- Prior art keywords
- alkyl
- aryl
- benzyl
- dioxide
- cycloalkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 194
- 102000003678 AMPA Receptors Human genes 0.000 title claims abstract description 26
- 108090000078 AMPA Receptors Proteins 0.000 title claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 212
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 212
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 76
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 73
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 64
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 386
- 125000003118 aryl group Chemical group 0.000 claims description 265
- 238000000034 method Methods 0.000 claims description 257
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 195
- -1 amino, thio Chemical group 0.000 claims description 189
- 150000002431 hydrogen Chemical group 0.000 claims description 180
- 229910052736 halogen Inorganic materials 0.000 claims description 174
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 168
- 125000003545 alkoxy group Chemical group 0.000 claims description 160
- 150000002367 halogens Chemical class 0.000 claims description 137
- 125000000623 heterocyclic group Chemical group 0.000 claims description 129
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 103
- 125000001424 substituent group Chemical group 0.000 claims description 96
- 125000000304 alkynyl group Chemical group 0.000 claims description 90
- 125000003342 alkenyl group Chemical group 0.000 claims description 85
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 68
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
- 125000001188 haloalkyl group Chemical group 0.000 claims description 61
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 50
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 45
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 44
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 39
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 34
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 34
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 28
- 208000035475 disorder Diseases 0.000 claims description 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
- 201000010099 disease Diseases 0.000 claims description 24
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 24
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 23
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 23
- 125000004429 atom Chemical group 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 22
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000002837 carbocyclic group Chemical group 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000001246 bromo group Chemical group Br* 0.000 claims description 14
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 13
- 230000006735 deficit Effects 0.000 claims description 13
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 12
- 208000024827 Alzheimer disease Diseases 0.000 claims description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
- 125000004445 cyclohaloalkyl Chemical group 0.000 claims description 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- 208000026139 Memory disease Diseases 0.000 claims description 11
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 9
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
- 210000003169 central nervous system Anatomy 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 230000015654 memory Effects 0.000 claims description 7
- 229940124530 sulfonamide Drugs 0.000 claims description 7
- LNVPUDKWUIASGN-UHFFFAOYSA-N 3-cyclohexyl-3,4,8,9-tetrahydro-2h-[1,4]dioxino[2,3-h][1,2,4]benzothiadiazine 1,1-dioxide Chemical compound N1C2=CC=C3OCCOC3=C2S(=O)(=O)NC1C1CCCCC1 LNVPUDKWUIASGN-UHFFFAOYSA-N 0.000 claims description 6
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 claims description 6
- 241000283690 Bos taurus Species 0.000 claims description 6
- 208000020358 Learning disease Diseases 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 201000003723 learning disability Diseases 0.000 claims description 6
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical group C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 208000000044 Amnesia Diseases 0.000 claims description 5
- 206010039966 Senile dementia Diseases 0.000 claims description 5
- 208000006011 Stroke Diseases 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 230000006984 memory degeneration Effects 0.000 claims description 5
- 208000023060 memory loss Diseases 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- PSOPMMVKRIPMTJ-UHFFFAOYSA-N 1-(sulfonylmethyl)piperazine Chemical compound O=S(=O)=CN1CCNCC1 PSOPMMVKRIPMTJ-UHFFFAOYSA-N 0.000 claims description 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
- WUMDYVDFUYYKMZ-UHFFFAOYSA-N 3-cyclohexyl-3,4,7,8-tetrahydro-2h-[1,4]dioxino[2,3-g][1,2,4]benzothiadiazine 1,1-dioxide Chemical compound N1C2=CC=3OCCOC=3C=C2S(=O)(=O)NC1C1CCCCC1 WUMDYVDFUYYKMZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 4
- 206010001605 Alcohol poisoning Diseases 0.000 claims description 4
- 206010003805 Autism Diseases 0.000 claims description 4
- 208000020706 Autistic disease Diseases 0.000 claims description 4
- 201000006474 Brain Ischemia Diseases 0.000 claims description 4
- LVRCEUVOXCJYSV-UHFFFAOYSA-N CN(C)S(=O)=O Chemical compound CN(C)S(=O)=O LVRCEUVOXCJYSV-UHFFFAOYSA-N 0.000 claims description 4
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 208000028017 Psychotic disease Diseases 0.000 claims description 4
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 230000032683 aging Effects 0.000 claims description 4
- 230000000747 cardiac effect Effects 0.000 claims description 4
- 206010008118 cerebral infarction Diseases 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 206010015037 epilepsy Diseases 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 208000014674 injury Diseases 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- 239000002581 neurotoxin Substances 0.000 claims description 4
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims description 4
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 4
- 201000009032 substance abuse Diseases 0.000 claims description 4
- 231100000736 substance abuse Toxicity 0.000 claims description 4
- 208000011117 substance-related disease Diseases 0.000 claims description 4
- 238000001356 surgical procedure Methods 0.000 claims description 4
- 230000008733 trauma Effects 0.000 claims description 4
- ZRRASWJMRDYRFA-UHFFFAOYSA-N 1-(3-cyclohexyl-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazin-7-yl)ethanol Chemical compound N1S(=O)(=O)C2=CC(C(O)C)=CC=C2NC1C1CCCCC1 ZRRASWJMRDYRFA-UHFFFAOYSA-N 0.000 claims description 3
- NAYYRCQJMRTILN-UHFFFAOYSA-N 3-cyclohexyl-7-[2-methoxy-4-(trifluoromethyl)phenyl]-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound COC1=CC(C(F)(F)F)=CC=C1C1=CC=C(NC(NS2(=O)=O)C3CCCCC3)C2=C1 NAYYRCQJMRTILN-UHFFFAOYSA-N 0.000 claims description 3
- KGNRLPYIJPANAS-UHFFFAOYSA-N 3-cyclohexyl-8-(2-methoxyphenyl)-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound COC1=CC=CC=C1C1=CC=CC2=C1S(=O)(=O)NC(C1CCCCC1)N2 KGNRLPYIJPANAS-UHFFFAOYSA-N 0.000 claims description 3
- GGMLWMOUORXJLT-UHFFFAOYSA-N 7-(2-chlorophenyl)-3-cyclohexyl-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound ClC1=CC=CC=C1C1=CC=C(NC(NS2(=O)=O)C3CCCCC3)C2=C1 GGMLWMOUORXJLT-UHFFFAOYSA-N 0.000 claims description 3
- DUSPWCCMTHFRRY-UHFFFAOYSA-N O=S(=O)NC1CCCCC1 Chemical compound O=S(=O)NC1CCCCC1 DUSPWCCMTHFRRY-UHFFFAOYSA-N 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- WZWQJRQCWCFUTM-UHFFFAOYSA-N morpholine-4-sulfonamide Chemical compound NS(=O)(=O)N1CCOCC1 WZWQJRQCWCFUTM-UHFFFAOYSA-N 0.000 claims description 3
- QDOQLKXQYLZYEA-UHFFFAOYSA-N (3-cyclohexyl-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazin-8-yl)methanol Chemical compound N1S(=O)(=O)C=2C(CO)=CC=CC=2NC1C1CCCCC1 QDOQLKXQYLZYEA-UHFFFAOYSA-N 0.000 claims description 2
- RTNBYRCCHKLPFQ-UHFFFAOYSA-N 1-(3-cyclohexyl-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazin-7-yl)ethanone Chemical compound N1S(=O)(=O)C2=CC(C(=O)C)=CC=C2NC1C1CCCCC1 RTNBYRCCHKLPFQ-UHFFFAOYSA-N 0.000 claims description 2
- QMOZKEWGXCGKHO-UHFFFAOYSA-N 1-ethoxybicyclo[2.2.1]hept-2-ene Chemical group C1CC2C=CC1(OCC)C2 QMOZKEWGXCGKHO-UHFFFAOYSA-N 0.000 claims description 2
- RWUDZOCZVQBJNI-UHFFFAOYSA-N 2,3,10,10a-tetrahydro-1h-pyrrolo[1,2-b][1,2,4]benzothiadiazine 5,5-dioxide Chemical compound N1C2=CC=CC=C2S(=O)(=O)N2C1CCC2 RWUDZOCZVQBJNI-UHFFFAOYSA-N 0.000 claims description 2
- JURGPCFAAKMAIA-UHFFFAOYSA-N 2-cyclohexyl-1,2,3,4-tetrahydroquinazoline-6-sulfonamide Chemical compound N1CC2=CC(S(=O)(=O)N)=CC=C2NC1C1CCCCC1 JURGPCFAAKMAIA-UHFFFAOYSA-N 0.000 claims description 2
- MOFJSTXFUSYCDO-UHFFFAOYSA-N 2-methyl-2,3-dihydro-1,3-benzoxazin-4-one Chemical compound C1=CC=C2OC(C)NC(=O)C2=C1 MOFJSTXFUSYCDO-UHFFFAOYSA-N 0.000 claims description 2
- AMZRLVJMBHMIPA-UHFFFAOYSA-N 2-phenyl-2,3-dihydro-1,3-benzoxazin-4-one Chemical compound O1C2=CC=CC=C2C(=O)NC1C1=CC=CC=C1 AMZRLVJMBHMIPA-UHFFFAOYSA-N 0.000 claims description 2
- BIVGFFFLVZMILM-UHFFFAOYSA-N 2-phenyl-2,3-dihydro-1h-quinazolin-4-one Chemical compound N1C2=CC=CC=C2C(=O)NC1C1=CC=CC=C1 BIVGFFFLVZMILM-UHFFFAOYSA-N 0.000 claims description 2
- ZQGCBOWEEAHZJP-UHFFFAOYSA-N 3-(2-methylpropyl)-8-piperidin-1-ylsulfonyl-2,3,4,5-tetrahydro-1$l^{6},2,5-benzothiadiazepine 1,1-dioxide Chemical compound C1=C2S(=O)(=O)NC(CC(C)C)CNC2=CC=C1S(=O)(=O)N1CCCCC1 ZQGCBOWEEAHZJP-UHFFFAOYSA-N 0.000 claims description 2
- UYRZSQPPZIJHEH-UHFFFAOYSA-N 3-(3-cyclohexyl-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazin-7-yl)phenol Chemical compound OC1=CC=CC(C=2C=C3S(=O)(=O)NC(NC3=CC=2)C2CCCCC2)=C1 UYRZSQPPZIJHEH-UHFFFAOYSA-N 0.000 claims description 2
- GVMZEULNBBKLON-UHFFFAOYSA-N 3-cyclohexyl-4-methyl-7-morpholin-4-ylsulfonyl-2,3-dihydro-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound C=1C=C2N(C)C(C3CCCCC3)NS(=O)(=O)C2=CC=1S(=O)(=O)N1CCOCC1 GVMZEULNBBKLON-UHFFFAOYSA-N 0.000 claims description 2
- ZJYBPAKREINUPO-UHFFFAOYSA-N 3-cyclohexyl-7-(2-methoxyphenyl)-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound COC1=CC=CC=C1C1=CC=C(NC(NS2(=O)=O)C3CCCCC3)C2=C1 ZJYBPAKREINUPO-UHFFFAOYSA-N 0.000 claims description 2
- PERVUQCEACNMMX-UHFFFAOYSA-N 3-cyclohexyl-7-pyrrolidin-1-ylsulfonyl-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound C=1C=C2NC(C3CCCCC3)NS(=O)(=O)C2=CC=1S(=O)(=O)N1CCCC1 PERVUQCEACNMMX-UHFFFAOYSA-N 0.000 claims description 2
- SJXMJUXZVDLBTM-UHFFFAOYSA-N 3-cyclohexyl-8-methyl-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound N1S(=O)(=O)C=2C(C)=CC=CC=2NC1C1CCCCC1 SJXMJUXZVDLBTM-UHFFFAOYSA-N 0.000 claims description 2
- RVSVPOUZDNHJSI-UHFFFAOYSA-N 3-cyclohexyl-n,n-diethyl-5-methyl-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound N1S(=O)(=O)C2=CC(S(=O)(=O)N(CC)CC)=CC(C)=C2NC1C1CCCCC1 RVSVPOUZDNHJSI-UHFFFAOYSA-N 0.000 claims description 2
- MAKFSUYZYPTPCS-UHFFFAOYSA-N 3-cyclohexyl-n-methyl-1,1-dioxo-n-phenyl-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound C=1C=C2NC(C3CCCCC3)NS(=O)(=O)C2=CC=1S(=O)(=O)N(C)C1=CC=CC=C1 MAKFSUYZYPTPCS-UHFFFAOYSA-N 0.000 claims description 2
- GXICUQFGNSKOGE-UHFFFAOYSA-N 3-cyclopropyl-7-piperidin-1-ylsulfonyl-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound C=1C=C2NC(C3CC3)NS(=O)(=O)C2=CC=1S(=O)(=O)N1CCCCC1 GXICUQFGNSKOGE-UHFFFAOYSA-N 0.000 claims description 2
- XFAUQNOCFCXERV-UHFFFAOYSA-N 3-methyl-7-piperidin-1-ylsulfonyl-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound C1=C2S(=O)(=O)NC(C)NC2=CC=C1S(=O)(=O)N1CCCCC1 XFAUQNOCFCXERV-UHFFFAOYSA-N 0.000 claims description 2
- YYPWDMFWDGAUPK-UHFFFAOYSA-N 4-oxo-2-(trifluoromethyl)-1h-quinazoline-6-sulfonamide Chemical compound N1=C(C(F)(F)F)NC(=O)C2=CC(S(=O)(=O)N)=CC=C21 YYPWDMFWDGAUPK-UHFFFAOYSA-N 0.000 claims description 2
- ZZLIOEBICMRZBJ-UHFFFAOYSA-N 5,5-dioxo-2,3,3a,4-tetrahydro-1h-pyrrolo[2,1-c][1,2,4]benzothiadiazine-7-sulfonamide Chemical compound N1S(=O)(=O)C2=CC(S(=O)(=O)N)=CC=C2N2CCCC21 ZZLIOEBICMRZBJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- WWEMWQKCUKUJHS-UHFFFAOYSA-N n,n,3-trimethyl-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound C1=C(S(=O)(=O)N(C)C)C=C2S(=O)(=O)NC(C)NC2=C1 WWEMWQKCUKUJHS-UHFFFAOYSA-N 0.000 claims description 2
- HDIWBVUJWJJWAJ-UHFFFAOYSA-N n,n-dimethyl-5,5-dioxo-2,3,3a,4-tetrahydro-1h-pyrrolo[2,1-c][1,2,4]benzothiadiazine-7-sulfonamide Chemical compound N1S(=O)(=O)C2=CC(S(=O)(=O)N(C)C)=CC=C2N2CCCC21 HDIWBVUJWJJWAJ-UHFFFAOYSA-N 0.000 claims description 2
- CASOHOKYBJSFPE-UHFFFAOYSA-N n-(3-cyclohexyl-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazin-7-yl)acetamide Chemical compound N1S(=O)(=O)C2=CC(NC(=O)C)=CC=C2NC1C1CCCCC1 CASOHOKYBJSFPE-UHFFFAOYSA-N 0.000 claims description 2
- WYQUJFKKCKVAMP-UHFFFAOYSA-N n-methyl-5,5-dioxo-2,3,3a,4-tetrahydro-1h-pyrrolo[2,1-c][1,2,4]benzothiadiazine-7-sulfonamide Chemical compound N1S(=O)(=O)C2=CC(S(=O)(=O)NC)=CC=C2N2CCCC21 WYQUJFKKCKVAMP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 37
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims 4
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims 4
- 150000008349 1,2,4-benzothiadiazines Chemical class 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
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- 229940095064 tartrate Drugs 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- SJZNRVUBNAJWQA-UHFFFAOYSA-N trimethyl(2h-triazol-4-yl)silane Chemical compound C[Si](C)(C)C1=CNN=N1 SJZNRVUBNAJWQA-UHFFFAOYSA-N 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/08—Antiepileptics; Anticonvulsants
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P25/32—Alcohol-abuse
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
- C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D285/24—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
- C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D285/24—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom
- C07D285/26—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals
- C07D285/28—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK22698 | 1998-02-18 | ||
| DK0226/98 | 1998-02-18 | ||
| PCT/DK1999/000070 WO1999042456A2 (en) | 1998-02-18 | 1999-02-18 | Novel compounds and their use as positive ampa receptor modulators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2320354A1 true CA2320354A1 (en) | 1999-08-26 |
Family
ID=8091151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002320354A Abandoned CA2320354A1 (en) | 1998-02-18 | 1999-02-18 | Novel compounds and their use as positive ampa receptor modulators |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP1071426A2 (xx) |
| JP (1) | JP2002504481A (xx) |
| CN (1) | CN1293665A (xx) |
| AU (1) | AU751384B2 (xx) |
| CA (1) | CA2320354A1 (xx) |
| EE (1) | EE200000468A (xx) |
| HU (1) | HUP0101280A3 (xx) |
| IL (1) | IL137720A0 (xx) |
| IS (1) | IS5581A (xx) |
| NO (1) | NO20004121L (xx) |
| NZ (1) | NZ506251A (xx) |
| PL (1) | PL342843A1 (xx) |
| RU (1) | RU2214405C2 (xx) |
| SK (1) | SK11892000A3 (xx) |
| TR (1) | TR200002427T2 (xx) |
| WO (1) | WO1999042456A2 (xx) |
| ZA (1) | ZA991301B (xx) |
Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7671200B2 (en) | 1999-10-27 | 2010-03-02 | Cytokinetics, Inc. | Quinazolinone KSP inhibitors |
| DE10004572A1 (de) * | 2000-02-02 | 2001-08-09 | Boehringer Ingelheim Pharma | Neue positive allosterische AMPA-Rezeptor Modulatoren (PAARM), Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| FR2812291B1 (fr) * | 2000-07-28 | 2002-12-13 | Adir | Nouveaux derives de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CN1314351A (zh) * | 2001-03-22 | 2001-09-26 | 刘志红 | 喹唑啉酮合成方法及具有抗癌作用的一类喹唑啉酮化合物 |
| TWI232863B (en) * | 2001-06-11 | 2005-05-21 | Akzo Nobel Nv | Benzoxazepine derivatives |
| WO2002102808A2 (en) | 2001-06-14 | 2002-12-27 | Akzo Nobel N.V. | (PYRIDO/THIENO)-[f]-OXAZEPIN-5-ONE DERIVATIVES AS POSITIVE MODULATORS OF THE AMPA RECEPTOR |
| CA2458388A1 (en) * | 2001-10-10 | 2003-04-17 | Neurosearch A/S | Novel benzothiazine derivatives, their preparation and use |
| MXPA04004815A (es) * | 2001-11-26 | 2005-02-17 | Cortex Pharma Inc | Compuestos de carbonilbenzoxazina para mejorar respuestas sinapticas, glutamatergicas. |
| FR2833956B1 (fr) * | 2001-12-21 | 2004-01-30 | Servier Lab | Nouveaux derives de benzothiazine et de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2833950B1 (fr) * | 2001-12-21 | 2005-12-16 | Servier Lab | Nouveaux derives de benzothiazine et de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2833955B1 (fr) | 2001-12-21 | 2004-01-30 | Servier Lab | Nouveaux derives de benzothiazine et de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2854634B1 (fr) * | 2003-05-05 | 2005-07-08 | Servier Lab | Nouveaux derives de thiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2856064B1 (fr) * | 2003-06-13 | 2005-08-19 | Servier Lab | Nouveaux derives de benzothiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2856065B1 (fr) * | 2003-06-13 | 2005-08-19 | Servier Lab | Nouveaux derives de benzothiazine et benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| JP2009513502A (ja) | 2003-07-02 | 2009-04-02 | エフ．ホフマン−ラ ロシュ アーゲー | アリールアミン置換キナゾリノン化合物 |
| AU2004270162B2 (en) | 2003-08-28 | 2010-05-13 | Nicox S.A. | Nitrosated ad nitrosylated diuretic compouds, compositions and methods of use |
| US7244843B2 (en) | 2003-10-07 | 2007-07-17 | Bristol-Myers Squibb Company | Modulators of serotonin receptors |
| FR2865474B1 (fr) * | 2004-01-26 | 2008-06-13 | Servier Lab | Nouveaux derives de benzothiazines fluorees, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2877338B1 (fr) | 2004-11-03 | 2007-01-26 | Servier Lab | Nouveaux derives de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2877342B1 (fr) | 2004-11-03 | 2007-01-26 | Servier Lab | Nouveaux derives de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2879201B1 (fr) | 2004-12-10 | 2007-02-16 | Servier Lab | Nouveaux derives de benzothiazine et benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| WO2006086464A2 (en) | 2005-02-10 | 2006-08-17 | Bristol-Myers Squibb Company | Dihydroquinazolinones as 5ht modulators |
| CA2597460A1 (en) | 2005-02-24 | 2006-08-31 | Nitromed, Inc. | Nitric oxide enhancing diuretic compounds, compositions and methods of use |
| GB0507298D0 (en) * | 2005-04-11 | 2005-05-18 | Novartis Ag | Organic compounds |
| TW200800959A (en) | 2005-06-10 | 2008-01-01 | Wyeth Corp | Piperazine-piperidine antagonists and agonists of the 5-HT1a receptor |
| MX2009007242A (es) | 2007-01-03 | 2009-09-02 | Cortex Pharma Inc | Compuesto de [1,2,3]-benzotriazinona 3-sustituida para mejorar respuestas sinapticas glutamatergicas. |
| TW200901974A (en) | 2007-01-16 | 2009-01-16 | Wyeth Corp | Compounds, compositions, and methods of making and using them |
| NZ582035A (en) | 2007-05-17 | 2012-03-30 | Cortex Pharma Inc | Di-substituted amides for enhancing glutamatergic synaptic responses |
| AU2008287445A1 (en) | 2007-08-10 | 2009-02-19 | Cortex Pharmaceuticals, Inc. | Bicyclic amides for enhancing glutamatergic synaptic responses |
| US8119632B2 (en) | 2007-08-10 | 2012-02-21 | Cortex Pharmaceuticals, Inc. | Bicyclic amide derivatives for enhancing glutamatergic synaptic responses |
| FR2933698A1 (fr) | 2008-07-09 | 2010-01-15 | Servier Lab | Nouveaux derives de benzothiadiazines cycloalkylees, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2943342B1 (fr) | 2009-03-20 | 2011-03-04 | Servier Lab | Nouveaux derives de benzothiadiazepines,leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| US8952034B2 (en) | 2009-07-27 | 2015-02-10 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
| FR2955107B1 (fr) * | 2010-01-08 | 2012-03-02 | Servier Lab | Nouveaux derives thiochromanes, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2955106B1 (fr) | 2010-01-08 | 2011-12-23 | Servier Lab | Nouveaux derives de benzothiadiazines cyclopropylees, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| AU2011272787B2 (en) | 2010-07-02 | 2015-06-18 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
| CN102958919A (zh) * | 2010-07-02 | 2013-03-06 | 霍夫曼-拉罗奇有限公司 | 新的四氢喹啉衍生物 |
| FR2964969B1 (fr) | 2010-09-16 | 2012-08-24 | Servier Lab | Nouveaux derives dihydrobenzoxathiazepines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| IT1402905B1 (it) * | 2010-11-29 | 2013-09-27 | Univ Degli Studi Modena E Reggio Emilia | Derivati di 1,2,4-benzotiadiazin 1,1-diossido, loro preparazione e loro impiego come modulatori allosterici del recettore ampa. |
| NZ716420A (en) | 2011-05-10 | 2017-05-26 | Gilead Sciences Inc | Fused heterocyclic compounds as sodium channel modulators |
| NO3175985T3 (xx) | 2011-07-01 | 2018-04-28 | ||
| TW201837023A (zh) | 2011-07-01 | 2018-10-16 | 美商基利科學股份有限公司 | 作為離子通道調節劑之稠合雜環化合物 |
| CN102977054A (zh) * | 2012-12-12 | 2013-03-20 | 中国药科大学 | 一类选择性α2A受体激动剂的治疗阿尔茨海默病用途 |
| JO3316B1 (ar) | 2013-05-30 | 2019-03-13 | Lilly Co Eli | مركبات 3، 4-داي هيدرو أيزو كوينولين -2(1h)-يل |
| CN105263924B (zh) | 2013-05-30 | 2018-10-19 | 爱杜西亚制药有限公司 | Cxcr7受体调节剂 |
| CN103275016B (zh) * | 2013-06-04 | 2015-03-11 | 温州医科大学附属第二医院 | 一种2-取代喹唑啉化合物的合成方法 |
| CA2915405A1 (en) | 2013-06-13 | 2014-12-18 | Veroscience Llc | Compositions and methods for treating metabolic disorders |
| CN103319381B (zh) * | 2013-06-14 | 2014-08-27 | 湖州康企药业有限公司 | 一种高纯度精磺胺的制备方法 |
| CN103772296B (zh) * | 2013-12-19 | 2015-06-17 | 安徽师范大学 | 一种喹唑啉衍生物的合成方法 |
| US10202368B2 (en) | 2014-12-01 | 2019-02-12 | Idorsia Pharmaceuticals Ltd. | CXCR7 receptor modulators |
| CN105294599B (zh) * | 2015-09-17 | 2017-09-22 | 三峡大学 | 一种噻二嗪类化合物及其不对称的合成方法 |
| CN106946920A (zh) * | 2017-04-05 | 2017-07-14 | 泰力特医药（湖北）有限公司 | 一种4‑氨基苯硼酸衍生物的制备方法 |
| WO2020253860A1 (zh) * | 2019-06-21 | 2020-12-24 | 江苏豪森药业集团有限公司 | 芳基磷氧化物类衍生物抑制剂、其制备方法和应用 |
| RU2726456C1 (ru) * | 2019-10-02 | 2020-07-14 | Общество с ограниченной ответственностью "Научно-исследовательский институт ХимРар" (ООО "НИИ ХимРар") | Ингибитор вируса гепатита В (ВГВ) |
| CN111100042B (zh) * | 2019-11-18 | 2022-05-31 | 苏州诚和医药化学有限公司 | 一种2-甲氧基-5-磺酰胺基苯甲酸的制备方法 |
| CN111018750B (zh) * | 2019-12-19 | 2022-05-27 | 苏州诚和医药化学有限公司 | 一种2,3-二甲氧基-5-磺酰胺基苯甲酸的制备新方法 |
| WO2024115797A2 (en) * | 2022-12-30 | 2024-06-06 | Aexon Labs. Inc. | Dihydro-quinazoline, -benzothiazine and -benzoxazine derivatives and use thereof as orexin receptors agonists for treating or preventing neurological diseases |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3275625A (en) * | 1966-09-27 | Derivatives of | ||
| NL296964A (xx) * | ||||
| FR1217929A (fr) * | 1958-03-03 | 1960-05-06 | Ciba Geigy | Procédé de préparation du 1,1-dioxyde de la 6-chloro-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine et de ses sels |
| GB863474A (en) * | 1958-08-13 | 1961-03-22 | Knud Abildgaard | Benzothiadiazine derivatives and their preparation |
| DE1125938B (de) * | 1960-02-12 | 1962-03-22 | Thomae Gmbh Dr K | Verfahren zur Herstellung von 7-Sulfamyl-3, 4-dihydro-1, 2, 4-benzothiadiazin-1, 1-dioxyden |
| GB946864A (en) * | 1960-05-06 | 1964-01-15 | Knud Abildgaard | Method for the production of 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxides |
| US3419552A (en) * | 1961-04-12 | 1968-12-31 | Lilly Co Eli | Preparation of substituted dihydrobenzothiadiazine-1,1-dioxides |
| CH475269A (de) * | 1962-04-19 | 1969-07-15 | Hans Voigt Chem Pharm Fabrik D | Verfahren zur Herstellung von 7-Sulfonamido-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyden |
| US3351595A (en) * | 1962-12-07 | 1967-11-07 | Ciba Geigy Corp | Derivatives of 3, 4-dihydro-2h-1, 2, 4-benzothiadiazine-1, 1-dioxide |
| US3311620A (en) * | 1963-05-31 | 1967-03-28 | Stanley C Bell | Fused ring benzothiadiazines |
| US3277086A (en) * | 1964-07-07 | 1966-10-04 | American Home Prod | 1, 2, 4-benzothiadiazine 1, 1-dioxides having a heterocyclic ring fused to the "b" face thereof |
| US4184039A (en) * | 1977-12-01 | 1980-01-15 | Paul Finkelstein | Benzothiadiazine 1, 1-dioxides |
| JPH07505411A (ja) * | 1992-04-15 | 1995-06-15 | ローン−プーラン・ロレ・ソシエテ・アノニム | ３，４−ジヒドロ−１ｈ−１，２，４−ベンゾチアジアジン−１，１−ジオキシド−２−カルボン酸誘導体，それらの製造およびそれらを含有する医学的生成物 |
| US5488049A (en) * | 1993-12-10 | 1996-01-30 | Fidia - Georgetown Institute For The Neuro-Sciences | Method of treating learning and memory disorders using benzothiadiazide derivatives as nootropic agents |
| FR2722502B1 (fr) * | 1994-07-12 | 1996-08-23 | Adir | Nouveau derive de benzothiadiazine, son procede depreparation et les compositions pharmaceutiques qui le contiennent |
| CA2242879C (en) * | 1996-01-29 | 2009-05-26 | The Regents Of The University Of California | Method for treating sexual dysfunctions |
| WO1998012185A1 (en) * | 1996-09-17 | 1998-03-26 | The Regents Of The University Of California | Benzothiadiazide derivatives and their use as allosteric up-modulators of the ampa receptor |
-
1999
- 1999-02-18 PL PL99342843A patent/PL342843A1/xx unknown
- 1999-02-18 JP JP2000532408A patent/JP2002504481A/ja not_active Withdrawn
- 1999-02-18 EE EEP200000468A patent/EE200000468A/xx unknown
- 1999-02-18 HU HU0101280A patent/HUP0101280A3/hu unknown
- 1999-02-18 SK SK1189-2000A patent/SK11892000A3/sk unknown
- 1999-02-18 CA CA002320354A patent/CA2320354A1/en not_active Abandoned
- 1999-02-18 WO PCT/DK1999/000070 patent/WO1999042456A2/en not_active Application Discontinuation
- 1999-02-18 AU AU25123/99A patent/AU751384B2/en not_active Ceased
- 1999-02-18 CN CN99804196A patent/CN1293665A/zh active Pending
- 1999-02-18 RU RU2000121882/04A patent/RU2214405C2/ru not_active IP Right Cessation
- 1999-02-18 TR TR2000/02427T patent/TR200002427T2/xx unknown
- 1999-02-18 NZ NZ506251A patent/NZ506251A/xx unknown
- 1999-02-18 IL IL13772099A patent/IL137720A0/xx unknown
- 1999-02-18 ZA ZA9901301A patent/ZA991301B/xx unknown
- 1999-02-18 EP EP99904730A patent/EP1071426A2/en not_active Withdrawn
-
2000
- 2000-08-04 IS IS5581A patent/IS5581A/is unknown
- 2000-08-17 NO NO20004121A patent/NO20004121L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1293665A (zh) | 2001-05-02 |
| NO20004121D0 (no) | 2000-08-17 |
| SK11892000A3 (sk) | 2001-02-12 |
| RU2214405C2 (ru) | 2003-10-20 |
| WO1999042456A2 (en) | 1999-08-26 |
| AU2512399A (en) | 1999-09-06 |
| ZA991301B (en) | 1999-09-13 |
| PL342843A1 (en) | 2001-07-16 |
| EE200000468A (et) | 2002-04-15 |
| HUP0101280A2 (hu) | 2001-10-28 |
| NO20004121L (no) | 2000-10-17 |
| IS5581A (is) | 2000-08-04 |
| JP2002504481A (ja) | 2002-02-12 |
| TR200002427T2 (tr) | 2001-01-22 |
| IL137720A0 (en) | 2001-10-31 |
| NZ506251A (en) | 2003-01-31 |
| WO1999042456A3 (en) | 1999-10-07 |
| AU751384B2 (en) | 2002-08-15 |
| HUP0101280A3 (en) | 2003-02-28 |
| EP1071426A2 (en) | 2001-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20080121 |